Hitchhiking Across America in the Digital Age

Using the latest ride-share apps, Christopher Bagley drove 4,000 miles with six different strangers in his passenger seat.

First there was Alexandra, a Romanian-born physics student who enlightened me about the finer points of bow hunting as we cruised past the Blue Ridge Mountains in Virginia. Then there was Cory, a chef and aspiring Buddhist from Tennessee who taught me the differences between good and bad collard greens when we stopped at a Mississippi diner. And later there was Stasa, a Slovenian bike-tour leader who helped pass the time on a traffic-clogged California freeway by explaining how she’d learned to speak seven languages. All three were complete strangers to me, but there they sat, in the passenger seat of my car, on different stages of my recent cross-country drive. Hitchhikers? Only in the digital sense: We were matched online and had vetted each other via e-mail, Google, and social media before agreeing to spend multiple hours together on the road.

“I would never hitchhike—way too sketchy,” said Alexandra, 22. But since the algorithms of a ride-sharing site had put us together, she didn’t hesitate to climb into my car at the appointed hour on the campus of James Madison University in Harrisonburg, Virginia. She was going to see her boyfriend at Virginia Tech, a few hours southwest along my route on I-81.

Given how quickly people have gotten used to renting out their spare bedrooms via Airbnb and hopping into whichever Uber vehicle happens to be closest, there’s little doubt that the long-distance ride-share concept is poised to catch on. Indeed, in Europe the market is already thriving: France’s leading ride-share site, BlaBlaCar, has 10 million members in 18 countries and last summer raised $100 million in financing.

For drivers and passengers, the benefits of ride-sharing are obvious: lower costs, reduced carbon dioxide emissions, and new connections with like-minded travelers going in the same direction. “You can actually meet really cool people, and it makes the ride go much faster,” said Stasa, who has used several sites in Italy and Germany and was trying Zimride for the first time. Alexandra, for her part, has taken at least 20 trips using Zimride and says it’s popular among college kids, but she notes that most Americans still either haven’t heard of ride-share platforms or remain wary of the idea. “My mother doesn’t know I’m doing this today,” she said.

Over the past few months alone, several new platforms launched in the U.S.—including Tripda and the German app Carpooling (which later ceased operations here, after it was purchased by the leading European company BlaBlaCar). In the meantime, while the sites attempt to build the critical mass of users that’s essential for them to work well, many U.S. ride-sharers still rely on Craigslist, that bastion of online randomness (and unfiltered freakiness), due to the lack of better options. But these days, no matter which method you use, Google, Facebook, and Instagram have made it a lot easier to reduce the odds of your passenger or driver being a drug trafficker, a psychopath, or a plain old bore.

My ride-sharing experiment was part of my recent move to California: I wanted to take my car from New York to L.A. and visit friends along the way, while avoiding long stretches of solo driving. I began by creating a profile on Zimride that included my vehicle description (new Prius!), music preferences (wide-ranging!), a short bio (non-creepy!), and a link to my Facebook page. I also posted the ride on Craigslist, where the first few responses hinted at the motley mix of passengers I’d be choosing from. A New York makeup artist wanted to accompany me all the way to Arizona—along with her several cats. A 20-year-old Danish backpacker and circus performer wrote in an e-mail, “I just wanna go west! I’m a good driver and have gas money! Are you up for an adventure?” I was, but our dates and routes didn’t match.

Through Zimride I managed to book Alexandra and one other rider—a smiley nursing student named Lizzie—along my route in Virginia. The whole process seemed encouragingly efficient and legit. Pickup spots were confirmed in advance via text messages; the website automatically suggested the passenger fees ($20 each for Alexandra and Lizzie, payable in cash or via linked PayPal accounts). To foster a feeling of trust and safety, passengers and drivers are encouraged to post reviews after every trip. Alexandra told me about an extra security measure she takes while in the car: She and her boyfriend stay connected on their phones via a GPS app called Glympse, which transmits her location to him, block by block. “He can track me at all times,” she said, adding half-jokingly, “right up to his doorstep.”

If Jack Kerouac were 25 years old today, would he create a BlaBlaCar profile and link it to his Instagram selfies with Allen Ginsberg?

After a lengthy stopover in Nashville, where I visited a college roommate (and wondered whether I should actually move to Nashville instead of L.A., especially after sampling the gourmet ice pops at Las Paletas), I continued west with my first Craigslist passenger: Cory, the 25-year-old Tennessean. He was starting what he called a spiritual journey, leaving behind a girlfriend and a job as a cook to walk the entire California coast with a backpack and a tent. With his impressive guitar and banjo skills (“standard for a hillbilly,” he joked) and his stories about his recent travels in Laos, he was the kind of guy who would probably hitchhike all the way across the country if people still did that. Since neither of us was in a hurry, we took the scenic route for the next three days, with stopovers in Memphis and Clarksdale, Mississippi; the sound track was mostly Cory’s bluegrass music and his running commentary on the proper Southern way to shoot a deer, barbecue a pig, and pickle a quail egg.

After dropping off Cory in Oklahoma City, I sped past Amarillo and then veered north for a passenger-free detour. I’d never explored the American Southwest, and I wasn’t going to miss the chance to see southern Utah and the Grand Canyon, even if the ride-share options there are next to nil due to the sparse populations. (In these astonishing landscapes, people are beside the point anyway.) At the foot of a mesa in Monument Valley, on a spectacularly clear November afternoon, my Native American guide taught me several off-color words in Navajo and told me about his 200 cousins, one of whom he had inadvertently married. At the Lipan Point overlook on the South Rim of the Grand Canyon, I spent my first half hour just staring into the vastness, while listening to the hushed conversations of the equally dumbstruck people around me. (As one fraternity guy said to another, “I mean, I knew it would be big, but I didn’t know it would be this big.”)

Once I made my way back to I-40 near Flagstaff, potential passengers began to materialize. I politely turned down a couple of nutty Arizona Craigslisters, including one person in Sedona who was eager to travel to San Diego with me but not eager to reveal his or her name, age, or gender. “I am a beautiful being of Light, exploring Space at this point in the Soul’s experience,” he or she wrote. Ultimately I offered my front seat to Tim, a 40-year-old web developer who was the less exciting choice but also less likely to be carrying LSD in his luggage. Tim was returning home to San Diego from a job in Phoenix and spent much of the ride filling me in on SoCal insider secrets, including the treacherous Ho Chi Minh trail—the best unmarked hike to Black’s surfing beach in La Jolla.

On the final leg of the trip, in Southern California, I got a good taste of how ride-sharing may work when it finally comes of age. Shortly after posting my ride from San Diego to L.A. on Zimride, I received requests from a half-dozen riders and chose two whose departure time was the same as mine (Stasa the Slovenian, and Myra, a speech pathology student). California, of course, is often the place where new technologies are invented and initially adopted; it’s also where last summer Uber and Lyft debuted their carpooling offshoots, Uberpool and Lyft Line, offering a local spin on the ride-sharing concept. Zimride, in fact, was launched by a co-founder of Lyft, John Zimmer, who in 2013 sold the company to Enterprise for undisclosed millions in order to focus on Lyft’s more popular and profitable taxi-like service. Despite my reliance on it for this trip, Zimride essentially closed its business to the general public in January, when it announced that it would limit its services to its “core” market: the university students and corporate employees whose schools and businesses have partnered with the company to create their own ride-share networks.

In December the prospects for American ride-sharing got a temporary boost when the successful Munich-based platform Carpooling—which has handled more than 50 million rides worldwide since its inception in 2001—announced that it was entering the U.S market. Previously, European companies were hesitant to launch in America because of geographical and economic differences thought to hamper demand: Gas is cheaper here, car ownership is more widespread, and city-to-city distances are often greater. But Carpooling CEO Markus Barnikel said he’d begun to notice “a tremendous shift in attitude in America. Many people in cities, especially young people, have much less interest in owning a vehicle. They want access to a car but don’t need to possess one as a status symbol.” In May, however, before Carpooling had a chance to build a significant customer base, its American expansion was shelved following its purchase by European leader BlaBlaCar, which has indicated no immediate plans to launch in the U.S. For now, the only thing that’s certain about the future of ride-sharing is that new apps and startups will continue to come and go—as they are wont to do—until one or more of them finally catches on.

Meanwhile, it’s clear that the classic American road trip has already been completely transformed by digital technology. On my nearly 4,000-mile coast-to-coast trip, I saw only a handful of people standing by the roadside with their thumbs out, but I spent a lot of time thinking about the adventure and romance we associate with hitchhiking, and what has been lost and gained in our constantly connected world. If Jack Kerouac were 25 years old today, would he create a BlaBlaCar profile and link it to his Instagram selfies with Allen Ginsberg?

Still, no matter how many devices you’ve got linked to each other via Bluetooth, there’s something about a long drive on the open road that keeps you unshakably fixed in the current place and time—hands on the steering wheel, ready for anything. In the end, plenty of memorable moments came about the old-fashioned way, with no help from my iPhone. In eastern Oklahoma, when Cory and I were craving some barbecue for lunch, we asked a local woman for advice. She tipped us off about Wild Horse Mountain Bar-B-Que, the ultimate ramshackle smokehouse in the town of Sallisaw, where about half of the other customers were hunters in head-to-toe camouflage. My $5 smoky beef sandwich ranks among my lifetime top three. It wasn’t until a few days later, when I looked up the restaurant online, that I discovered it had 4 stars on Yelp.